Baeyer-Villiger-including domino two-step oxidations of β-O-substituted primary alcohols: Reflection of the migratory aptitudes of O-substituted alkyl group in the outcome of the reaction

Following the recent development of the one-pot two-step oxidation protocol for primary β-alkoxy alcohols, additional primary β-oxy alcohols were examined under similar conditions. The outcome of these reactions closely follows the migratory aptitudes of the related α-oxy-alkyls in Baeyer-Villiger oxidation vs. that of hydrogen. Thus, these experiments helped to establish the correct order of these aptitudes for α-oxy-alkyls. Furthermore, in the case of primary β,β-dialkoxyalcohols, the formation of dialkoxymethyl formates by the domino oxidation reaction was followed by secondary reactions, forming a number of interesting products.